936251-92-2Relevant academic research and scientific papers
The nature of the catalytically active species in olefin dioxygenation with PhI(OAc)2: Metal or proton?
Kang, Yan-Biao,Gade, Lutz H.
supporting information; experimental part, p. 3658 - 3667 (2011/05/03)
Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)2 as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant
Seayad, Jayasree,Seayad, Abdul Majeed,Chai, Christina L. L.
supporting information; experimental part, p. 1412 - 1415 (2010/06/13)
(Figure Presented) Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently In the presence of PhI(OAc)2 as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds In 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.
Bis(NHC)-palladium(II) complex-catalyzed dioxygenation of alkenes
Wang, Wenfeng,Wang, Feijun,Shi, Min
experimental part, p. 928 - 933 (2010/05/01)
Bis(NHC)-Pd(II) complexes derived from l,l'-binaphthyl-2,2'-diamine (BINAM) were successfully first used to catalyze the dioxygenation of alkenes under mild conditions tolerant of air and moisture. Cationic NHC-Pd2+ diaquo complex 1e showed the highest catalytic activity to give 1,2dioxygenation products with good syn-diastereoselectivity for 1,2-disubstituted alkenes.
Palladium-catalyzed olefin dioxygenation
Li, Yang,Song, Datong,Dong, Vy M.
, p. 2962 - 2964 (2008/09/20)
A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and PhI(OAc)2 as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An 18O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates. Copyright
Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols
Tiecco, Marcello,Testaferri, Lorenzo,Marini, Francesca,Sternativo, Silvia,Santi, Claudio,Bagnoli, Luana,Temperini, Andrea
, p. 5482 - 5489 (2008/01/07)
A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a δ-carbon radical adds intramolecularly to the carbonyl group of an aldeh
